Bitcoin Billionaire Michael Saylor Settles $40 Million Tax Fraud Lawsuit

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Mayur Joshi
Mayur Joshihttp://www.mayurjoshi.com
Mayur Joshi is a contributing editor to Regtechtimes, he is recognized for his insightful reporting and analysis on financial crimes, particularly in the realms of espionage and sanctions. Mayur's expertise extends globally, with a notable focus on the sanctions imposed by OFAC, as well as those from the US, UK, and Australia. He is also regular contributor on Geopolitical subjects and have been writing about China. He has authored seven books on financial crimes and compliance, solidifying his reputation as a thought leader in the industry. One of his significant contributions is designing India's first certification program in Anti-Money Laundering, highlighting his commitment to enhancing AML practices. His book on global sanctions further underscores his deep knowledge and influence in the field of regtech.
Billionaire bitcoin bull and MicroStrategy co-founder Michael Saylor has agreed to pay $40 million to settle a lawsuit alleging he committed massive tax fraud by lying to authorities for years about where he lived. The Washington DC district attorney’s office announced this settlement on Monday.

Allegations of Massive Tax Evasion

DC prosecutors accused Saylor and MicroStrategy of evading more than $25 million in local income taxes from 2005 to 2022 through falsified records and statements. Saylor allegedly claimed to live in Florida or Virginia, while actually residing in a luxury waterfront penthouse in the capital’s prestigious Georgetown neighborhood.
Saylor did not admit to any wrongdoing in the settlement. “Florida remains my home today, and I continue to dispute the allegation that I was ever a resident of the District of Columbia,” he said in a statement. He explained that he settled the matter to avoid the continued burdens of litigation on his friends, family, and himself.

Luxurious Lifestyle of Michael Saylor

The DC district attorney’s office asserted that Saylor had spent millions to buy three luxury condo units with the intent of combining them into a 7,000-square-foot residence overlooking the Potomac River from 2006 to 2008. He allegedly continued living in the district aboard one of his yachts while renovations on his planned residence, dubbed “Trigate,” were underway.

Michael Saylor’s own social media posts played a significant role in the amended complaint against him, providing evidence that contradicted his claims of living in Florida or Virginia. Prosecutors cited these posts to illustrate that Saylor actually resided in Washington, DC, thereby supporting their allegations of tax fraud.

March 2012 Facebook Post of Michael Saylor

In March 2012, Michael Saylor posted a photo on Facebook with the caption “view from my Georgetown balcony this morning.” This post indicated that he was living in Georgetown, a well-known neighborhood in Washington, DC, rather than in Florida or Virginia as he had claimed. The photo and its caption were seen as direct evidence of his residency in the District, undermining his statements about living elsewhere.

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September 2012 Facebook Post of Michael Saylor

A few months later, in September 2012, Saylor made another revealing post. He wrote, “Gazing wistfully at my future home while I wait for James to crack the whip on the contractors and herd the cats. I wonder if Tony Stark would be so patient….” This post not only mentioned his ongoing involvement in the renovation of a property in Georgetown but also referenced “James,” who was identified as the penthouse’s architect, James Augustus Seymour Van Wynen. The casual tone and specific details about the renovation project further suggested Saylor’s deep personal connection to the residence.

Implications of the Social Media Evidence

These social media posts were critical in building the case against Saylor. They provided tangible evidence that he was physically present in Washington, DC, during the times he claimed to reside in other states. By openly discussing his Georgetown property and daily activities there, Saylor inadvertently provided prosecutors with key information that helped establish his true residency.

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Reaction from the Authorities

DC’s attorney general Brian Schwalb described the settlement as the “largest income tax fraud recovery in DC history.” He emphasized, “No one in the District of Columbia is above the law, no matter how wealthy or powerful they may be.”
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MicroStrategy shares were up 8% to approximately $1,625 per share in early trading Monday. Despite stepping down as MicroStrategy’s CEO in 2022, Michael Saylor remains a major proponent of bitcoin. His personal fortune has swelled alongside the significant surge in the price of bitcoin, with Forbes estimating his net worth at $4.8 billion as of Monday.
The Post reached out to MicroStrategy for further comment, but neither Michael Saylor nor MicroStrategy admitted to any wrongdoing or violations of the law in the settlement, the company said in a filing. The company will not be obligated to make any contribution to the settlement payment.
The lawsuit and subsequent settlement highlight the ongoing scrutiny faced by high-profile executives and the importance of adhering to tax regulations, regardless of wealth or status. This case serves as a reminder that the legal system holds everyone accountable, reinforcing the principle that no one is above the law.
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